66164-07-6 Usage
Description
DESMETHYL LOPERAMIDE, also known as N-Desmethyl-loperamide (dLop), is a major metabolite of the opiate Loperamide. It is a monocarboxylic acid amide with the chemical structure of the methylamide of 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanoic acid. DESMETHYL LOPERAMIDE is an off-white solid that, like Loperamide, selectively activates μ opioid receptors in the periphery and is a substrate of the ATP-dependent efflux transporter, P-glycoprotein. This results in restricted passage through the blood-brain barrier for both the parent compound and the metabolite. DESMETHYL LOPERAMIDE can be analyzed in biological samples using various methods.
Uses
Used in Pharmaceutical Applications:
DESMETHYL LOPERAMIDE is used as an active metabolite for its peripheral μ opioid receptor activation, which contributes to the overall efficacy of Loperamide in treating diarrhea and other gastrointestinal disorders. Its restricted passage through the blood-brain barrier minimizes the risk of central nervous system side effects, such as addiction and respiratory depression.
Used in Research and Analysis:
DESMETHYL LOPERAMIDE serves as a subject of study in various research fields, including pharmacology, drug metabolism, and drug transport. Its analysis in biological samples is essential for understanding the pharmacokinetics, pharmacodynamics, and potential drug-drug interactions involving Loperamide and its metabolites.
Used in Drug Development:
DESMETHYL LOPERAMIDE may be utilized in the development of new drugs with improved efficacy and safety profiles. Understanding its properties and interactions with biological systems can guide the design of novel therapeutic agents targeting the μ opioid receptors for various medical conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 66164-07-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,1,6 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 66164-07:
(7*6)+(6*6)+(5*1)+(4*6)+(3*4)+(2*0)+(1*7)=126
126 % 10 = 6
So 66164-07-6 is a valid CAS Registry Number.
InChI:InChI=1/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)
66164-07-6Relevant articles and documents
A high-yield route to synthesize the P-glycoprotein radioligand [ 11C]N-desmethyl-loperamide and its parent radioligand [ 11C]loperamide
Wang, Min,Gao, Mingzhang,Zheng, Qi-Huang
, p. 5259 - 5263 (2013/09/23)
N-Desmethyl-loperamide and loperamide were synthesized from α,α-diphenyl-γ-butyrolactone and 4-(4-chlorophenyl)-4- hydroxypiperidine in five and four steps with 8% and 16% overall yield, respectively. The amide precursor was synthesized from 4-bromo-2,2- diphenylbutyronitrile and 4-(4-chlorophenyl)-4-hydroxypiperidine in 2 steps with 21-57% overall yield. [11C]N-Desmethyl-loperamide and [ 11C]loperamide were prepared from their corresponding amide precursor and N-desmethyl-loperamide with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 20-30% and 10-15% radiochemical yields, respectively, based on [11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.
